I have yet to win 100 games close a couple of times, so may not be qualified to weigh in , however there are a few things not mentioned that lead me to believe it's unlikely.
first in winning the 100 games the team in question has likely beat several sub par teams . in the playoffs the competition is revved up.
also if two or three teams have 100 win seasons one or two of them will not get a ring.
I had 99 wins twice but lost both times because more experienced manager beat me.
anyway just food for thought